1. Field of the Invention
A great deal of research has been conducted to develop agents for the control of bacterial and protozoal infections of poultry, swine and cattle. Thus, compounds and methods for controlling colibacillosis, pasteurellosis and salmonellosis in cattle, chickens, and swine, coccidiosis in chickens, as well as swine dysentery, have been the subject of extended research for many years.
2. Description of the Prior Art
In the prior art, British Pat. No. 1,285,932, published Aug. 16, 1972, teaches substituted 5-nitrofuran compounds, including 5-amino-4-cyano-1-methyl-3-(5-nitro-2-furyl)pyrazole, methods for preparation of the compounds, and medicaments containing the substituted nitrofurans as the active ingredient. The compounds are taught as possessing activity as antimicrobial, anthelmintic and antiprotozoal agents, and also as being active as coccidiostats, trypanocides, and antimalarial agents.
Also in the prior art is British Pat. No. 1,363,323, published Aug. 14, 1974, which teaches 2-(5-nitro-2-imidazolyl)pyrimidines, and methods for their preparation. The compounds are taught as being active as trichomonacides, bactericides, and antifungals, as well as being useful for the treatment of vaginal infections.
Tomcufcik et al., U.S. Pat. No. 3,452,034 (June 24, 1969), teach substituted 2-(1,3,4-thiadiazol-2-yl)-4(5)-nitroimidazoles and the preparation thereof. The compounds are taught as being useful as antibacterials, amoebicides, trichomonacides, and coccidiostats.
Papaioannou, U.S. Pat. No. 3,682,942 (Aug. 8, 1972), teaches methods of preparing 2-(2-amino-1,3,4-thiadiazol-3-yl)-1-substituted-5-nitroimidazoles. The products are taught as being useful for the control of bacterial, parasitic, and protozoal infections in poultry and animals. In particular, the compounds are said to be effective against Trichomonas vaginalis and Salmonella gallinarum infections in poultry and animals, as described by Berkelhammer et al., U.S. Pat. No. 3,452,035 (June 24, 1969).
In addition, a series of 5-nitroimidazoles, substituted in the 2-position by heterocyclic ring systems, is disclosed by Rufer et al., Progr. Antimicrob. Anti-cancer Chemother., Proc. Int. Congr. Chemother., 6th 1969 (Pub. 1970), 1, 145-8. (Univ. Park Press: Baltimore, Maryland); Chem. Abstr. 74, 141632x (1971). These authors teach the compounds as being active against Trichomonas vaginalis in vitro.
Also in the prior art is Howarth et al., U.S. Pat. No. 3,682,953 (Aug. 8, 1972), directed to substituted 3-(5-nitro-2-furyl)pyrazoles and pharmaceutically-acceptable acid addition salts thereof, and to pharmaceutical and feedstuff compositions containing the compounds, as well as to methods for the treatment of microbial infections in mammals and to methods of protecting organic material against microbial attack using the claimed compounds. The compounds are alleged to have antibacterial, anthelmintic, antiprotozoal, coccidiostatic, trypanocidal, and antimalarial activity.
Another patent, Howarth et al., U.S. Pat. No. 3,682,956 (Aug. 8, 1972), is directed to 5-amino-4 -carbamoyl-3-(5-nitro-2-furyl)pyrazoles taught as having antimicrobial activity. The compounds are taught as being used in the same manner as described by Howarth et al., U.S. Pat. No. 3,682,953, supra.
Also in the prior art is Howarth, U.S. Pat. No. 3,716,555 (Feb. 13, 1973), directed to derivatives of 3-(5-nitro-2-furyl)pyrazole, which compounds are taught as having antimicrobial properties and to be used in the same manner as described in the above two Howarth et al. patents.
Sarett et al., U.S. Pat. No. 3,719,759 (Mar. 6, 1973), is directed to antiprotozoal compositions containing nitroimidazoles. The nitroimidazole compounds taught include 1-substituted-2-aryl-5-nitroimidazoles, wherein aryl represents phenyl or naphthyl, substituted or unsubstituted, and the 1-substituent can be lower alkyl. The compounds are taught as being effective against protozoal infections such as histomoniasis, trichomoniasis, amoebiasis, and trypanosomiasis; as well as against helminths such as Heterakis and Ascarid species; bacteria such as Salmonella sp., Streptococcus sp., and Escherichia coli.; and pleuro pneumonia-like organisms (PPLO).
In addition, Sarett et al., U.S. Pat. No. 3,399,211 (Aug. 27, 1968), teach methods for preparing the compounds utilized in the antiprotozoal compositions of U.S. Pat. No. 3,719,759, discussed supra.
Another prior art reference is Japanese Pat. No. 73-39935, also identified by Derwent No. 74115U, directed to the preparation of 3-(5-nitro-2-furyl)pyrazole derivatives, taught as being useful as fungicides, chemotherapeutics, antiseptics, and food additives.
The compounds described in the prior art set forth above differ significantly structurewise from those of the instant application.